A visible light-driven Minisci-type reaction with N-hydroxyphthalimide esters

A visible light-promoted protocol for the redox-neutral coupling of N-hydroxyphthalimide esters with different n-heterocyclic compounds is described. the reaction proceeds through an alkyl radical intermediate generated by reductive decarboxylation of n-hydroxyphthalimide esters. in contrast to the original minisci protocol, polyalkylation can largely be avoided. mechanistic investigations revealed a radical chain mechanism which in some cases can proceed even if no photocatalyst is added. this valuable and functional group-tolerant reaction produces substituted heterocycles in moderate to excellent yield. the use of inexpensive starting materials and leds as the light source are key features of this c–c bond formation

Synthesis of Benzhydryl-Substituted Amines by Silanolate-Mediated Aldimine Arylation with Functionalized Aryl Nucleophiles Released from Diazene-Based Reagents

A transition-metal-free protocol for the arylation of N-phenyl- and N-benzoyl-substituted, benzaldehyde-derived imine derivatives with functionalized aryl pronucleophiles is reported. The aryl nucleophiles are released from silicon-protected aryl-substituted diazenes by desilylation with potassium trimethylsilanolate concomitant with the loss of dinitrogen. A broad range of functional groups is tolerated in the aryl nucleophile but, depending upon their electronic effect, require specific groups at the imine nitrogen atom